Detail

Varenicline

Description

Name: Varenicline
Type: small molecule
Groups: Array
Indication: For use as an aid in smoking cessation.
Accession Number: DB01273 ( DB01273)
Description: Varenicline is a prescription medication used to treat smoking addiction. This medication is the first approved nicotinic receptor partial agonist. Specifically, varenicline is a partial agonist of the alpha4/beta2 subtype of the nicotinic acetylcholine receptor. In addition it acts on alpha3/beta4 and weakly on alpha3beta2 and alpha6-containing receptors. A full agonism was displayed on alpha7-receptors. On March 9, 2015, the U.S. Food and Drug Administration warned that Varenicline, in the form of Pfizer Inc's quit-smoking drug, Chantix, has been associated with seizures and that some patients who drink while taking the drug may become aggressive or black out. Pfizer is conducting an additional safety study of the drug, results of which are expected in late 2015. The FDA said it is keeping the black box in place at least until the results of the trial are announced.
Structure:
Prescription Products:
NameDosageStrengthRouteMarketing StartMarketing EndCountry
Champixtablet0.5 mgoral11-04-2007Canada
Champixtablet1.0 mgoral11-04-2007Canada
ChantixkitArrayArray10-05-2006US
Chantixtablet, film coated1 mg/1oral23-02-2012US
ChantixkitArrayArray10-05-2006US
Chantixtablet, film coated.5 mg/1oral10-05-2006US
ChantixkitArrayArray10-05-2006US
Chantixtablet, film coated1 mg/1oral10-05-2006US
Chantixtablet, film coated.5 mg/1oral10-05-2006US
ChantixkitArrayArray10-05-2006US
Chantixtablet, film coated1 mg/1oral10-05-2006US
Chantixtablet, film coated.5 mg/1oral10-05-2006US
Chantixtablet, film coated.5 mg/1oral10-05-2006US
Chantixtablet, film coated1 mg/1oral10-05-2006US
ChantixkitArrayArray10-05-2006US
ChantixkitArrayArray01-09-2006US
Chantixtablet, film coated1 mg/1oral01-09-2006US
Chantixtablet, film coated.5 mg/1oral28-12-2011US
Chantixtablet, film coated1 mg/1oral23-02-2012US
Gd-vareniclinetablet0.5 mgoral01-01-1970Canada
Gd-vareniclinetablet1.0 mgoral01-01-1970Canada

Generic Prescription Products: Not Available
Over the Counter Products: Not Available
International Brands
  • No Brands

Brand Names
  • No Brands

Brand Mixtures
Brand NameIngredients
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChantixVarenicline
ChampixVarenicline
ChampixVarenicline
Gd-vareniclineVarenicline
Gd-vareniclineVarenicline

Categories
  • Nicotinic Agonists

Pharmacology

Indication: For use as an aid in smoking cessation.
Pharmacodynamics: Not Available
Mechanism of action: Varenicline is an alpha-4 beta-2 neuronal nicotinic acetylcholine receptor partial agonist. The drug shows high selectiviyty for this receptor subclass, relative to other nicotinic receptors (>500-fold alpha-3 beta-4, >3500-fold alpha-7, >20,000-fold alpha-1 beta gamma delta) or non-nicotinic receptors and transporters (>2000-fold). The drug competitively inhibits the ability of nicotine to bind to and activate the alpha-4 beta-2 receptor. The drug exerts mild agonistic activity at this site, though at a level much lower than nicotine; it is presumed that this activation eases withdrawal symptoms.
Absorption: Not Available
Volume of distribution: Not Available
Protein binding: Less than 20%.
Metabolism: Not Available
Route of elimination: Varenicline undergoes minimal metabolism, with 92% excreted unchanged in the urine. Renal elimination of varenicline is primarily through glomerular filtration along with active tubular secretion possibly via the organic cation transporter, OCT2.
Half life: The elimination half-life of varenicline is approximately 24 hours
Clearance: Not Available
Toxicity: Not Available
Affected organisms
  • Not Available

SNP Mediated Adverse Drug Reactions
  • Not Available

Pharmacoeconomics

Manufacturers:
  • Not Available

Packagers:
Dosage forms
FormRouteStrength
Tabletoral0.5 mg
Tabletoral1.0 mg
Kit
Tablet, film coatedoral.5 mg/1
Tablet, film coatedoral1 mg/1

Prices
Unit descriptionCostUnit
Chantix 0.5 mg tablet$2.56tablet
Chantix 1 mg cont month pak$2.56each
Chantix 1 mg tablet$2.61tablet
Chantix Continuing Month Pak 56 1 mg tablet Disp Pack$148.5disp
Chantix Starting Month Pak 0.5 mg X 11, 1 mg X 42 Disp Pack$148.5disp

Patents
CountryPatent NumberApprovedExpires (estimated)
2316921Canada2004-12-072018-11-13
2525874Canada2007-11-272024-05-07
6410550United States2000-05-102020-05-10
7265119United States2002-08-032022-08-03

Interactions

Drug Interactions
DrugInteraction
BupropionThe serum concentration of Varenicline can be increased when it is combined with Bupropion.
CimetidineThe serum concentration of Varenicline can be increased when it is combined with Cimetidine.
CiprofloxacinThe serum concentration of Varenicline can be increased when it is combined with Ciprofloxacin.
EthanolThe risk or severity of adverse effects can be increased when Varenicline is combined with Ethanol.
FamotidineThe serum concentration of Varenicline can be increased when it is combined with Famotidine.
GemifloxacinThe serum concentration of Varenicline can be increased when it is combined with Gemifloxacin.
LevofloxacinThe serum concentration of Varenicline can be increased when it is combined with Levofloxacin.
MoxifloxacinThe serum concentration of Varenicline can be increased when it is combined with Moxifloxacin.
NicotineThe risk or severity of adverse effects can be increased when Varenicline is combined with Nicotine.
NizatidineThe serum concentration of Varenicline can be increased when it is combined with Nizatidine.
NorfloxacinThe serum concentration of Varenicline can be increased when it is combined with Norfloxacin.
OfloxacinThe serum concentration of Varenicline can be increased when it is combined with Ofloxacin.
RanitidineThe serum concentration of Varenicline can be increased when it is combined with Ranitidine.
SparfloxacinThe serum concentration of Varenicline can be increased when it is combined with Sparfloxacin.
TrimethoprimThe serum concentration of Varenicline can be increased when it is combined with Trimethoprim.

Food Interactions:
  • Not Available

Taxonomy

Kingdom: Organic compounds
Super Class: Not Available
Class: Not Available
Sub Class: Not Available
Direct Parent: Not Available
Alternative Parents:
  • Aralkylamines
  • Azacyclic compounds
  • Azepines
  • Dialkylamines
  • Heteroaromatic compounds
  • Hydrocarbon derivatives
  • Indanes
  • Piperidines
  • Pyrazines
  • Quinoxalines

substituent:
  • Amine
  • Aralkylamine
  • Aromatic heteropolycyclic compound
  • Azacycle
  • Azepine
  • Benzazepine
  • Benzenoid
  • Heteroaromatic compound
  • Hydrocarbon derivative
  • Indane
  • Organonitrogen compound
  • Piperidine
  • Pyrazine
  • Quinoxaline
  • Secondary aliphatic amine
  • Secondary amine

References

Synthesis Reference: Vinod Kumar Kansal, Suhail Ahmad, Amit Gupta, "PROCESSES FOR THE PREPARATION OF VARENICLINE AND INTERMEDIATES THEREOF." U.S. Patent US20090318695, issued December 24, 2009.
General Reference: # Jorenby DE, Hays JT, Rigotti NA, Azoulay S, Watsky EJ, Williams KE, Billing CB, Gong J, Reeves KR: Efficacy of varenicline, an alpha4beta2 nicotinic acetylcholine receptor partial agonist, vs placebo or sustained-release bupropion for smoking cessation: a randomized controlled trial. JAMA. 2006 Jul 5;296(1):56-63. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16820547 # Mihalak KB, Carroll FI, Luetje CW: Varenicline is a partial agonist at alpha4beta2 and a full agonist at alpha7 neuronal nicotinic receptors. Mol Pharmacol. 2006 Sep;70(3):801-5. Epub 2006 Jun 9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16766716 # Obach RS, Reed-Hagen AE, Krueger SS, Obach BJ, O'Connell TN, Zandi KS, Miller S, Coe JW: Metabolism and disposition of varenicline, a selective alpha4beta2 acetylcholine receptor partial agonist, in vivo and in vitro. Drug Metab Dispos. 2006 Jan;34(1):121-30. Epub 2005 Oct 12. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16221753 # Coe JW, Brooks PR, Vetelino MG, Wirtz MC, Arnold EP, Huang J, Sands SB, Davis TI, Lebel LA, Fox CB, Shrikhande A, Heym JH, Schaeffer E, Rollema H, Lu Y, Mansbach RS, Chambers LK, Rovetti CC, Schulz DW, Tingley FD 3rd, O'Neill BT: Varenicline: an alpha4beta2 nicotinic receptor partial agonist for smoking cessation. J Med Chem. 2005 May 19;48(10):3474-7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15887955 # Kuehn BM: FDA speeds smoking cessation drug review. JAMA. 2006 Feb 8;295(6):614. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16467225
External Links:
ResourceLink
RxListhttp://www.rxlist.com/cgi/generic/chantix.htm
Drugs.comhttp://www.drugs.com/cdi/varenicline.html

ATC Codes:
  • Array

AHFS Codes:
  • Not Available

MSDS: Download
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